Diisobutylaluminumhydride → HCID 58764268, compound

HRID 859702Notes

Reaction equation

HRID 859702 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]2[N:13]=[CH:12][CH:11]=[N:10][N:9]2[CH:14]=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[N:10]1[N:9]2[CH:14]=[C:6]([CH:4]=[O:3])[N:7]=[C:8]2[N:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 21225700Diisobutylaluminumhydride2×HCID 58764108HCID 58764108, compound

Product 1

HCID 58764268HCID 58764268, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of imidazo[1,2-b][1,2,4]triazine-6-carboxylic acid ethyl ester (500 mg, 2.6 mmol, from step 1 above) in CH2Cl2 (15 mL) cooled to −78° C. was added diisobutylaluminum hydride (2.6 mL, 1.5 M in toluene). The reaction was stirred for one hour, and then extra diisobutylaluminum hydride (1 mL, 1.5 M) was added. After 20 more minutes, the cold reaction was quenched with EtOAc (10 mL), and then MeOH (10 mL). After the reaction had warmed to room temperature, 30 mL of 0.3 M HCl was added. The layers were separated. The aqueous phase was extracted three times with 10 mL of CH2Cl2. After the organic layers were combined and dried over MgSO4, the solids were removed by filtration. The organic liquid was concentrated by rotary evaporation, and the resulting oil was chromatographed (40 g SiO2, 50 to 100% EtOAc in hexanes) to give the desired product (47 mg, 12%).

Workup

  1. customAfter 20 more minutes, the cold reaction
  2. customwas quenched with EtOAc (10 mL)
  3. addition30 mL of 0.3 M HCl was added
  4. customThe layers were separated
  5. extractionThe aqueous phase was extracted three times with 10 mL of CH2Cl2
  6. dry with materialdried over MgSO4
  7. customthe solids were removed by filtration
  8. concentrationThe organic liquid was concentrated by rotary evaporation
  9. customthe resulting oil was chromatographed (40 g SiO2, 50 to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-94b4dae7baba454f88ca08ea98e3764b
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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